Oxidative coupling of thiols to disulfides in solution radiation with Trimethylammonium Fluorochromate(VI), [(CH3)3NH[CrO3F], on Silica Gel
Subject Areas : Journal of the Iranian Chemical Research
1 - Department of Chemistry, Faculty of Science, Imam Khomeini International University, Qazvin,
Iran
Keywords: Oxidation, Trimethylammonium fluorochromate(VI), Heterogeneous oxidants, Silica gel,
Abstract :
A mild and efficient method for the oxidative coupling of thiols by trimethylammonium fluorochromate(TriMFC) in solution is reported. Trimethylammonium fluorochromate is efficient and new reagent, whichprepares easily and oxidizes thiols to the corresponding disulfides quickly. The reactions perform cleanly andcontrolled to stop at the disulfide stage without over-oxidation side products.
[1] L.F. Fieser, M Fieser Ragents for Organic Synthesis, Wiley, New York, 1967.
[2] D.C. Jocelyn, Biochemistry of the Thiol Group, Academic Press, New York, 1992.
[3] G. Capozzi, G. Modena, S. Patai, The Chemistry of the thiol Group,Wiley, New York, 1974.
[4] J. Lam, H. Bildose, L.P Christensen, T. Thomsen, Acta Chem Scand. 5 (1989) 43 - 799.
[5] V. Srivastav, R. Gupta and R.R Guptam, Ind J Chem. 6 (2000) 39B-223.
[6] W.A. Pryor, D.F. Church, C. K. Govindan, G. Crank, synthetic utility and toxicological implications J.
Org. Chem. 47 (1982) 156–159.
[7] L Holbrook, Handbook of Petroleum Refining Processes, McGraw Hill, RA Meyers (Ed) New York,
1996.
[8] A. Leitao, C. Costa, A. Rodrigues, Chem Eng Sci. 9 (1987) 42-2291.
[9] E.P. Papadopoulos, A. Jarrar, C. H. Issidoides, J Org Chem. 10 (1966) 31- 615.
[10] C. Lopez, A. Conzales, F.P. Cossio, C. Palomo, Synth Commun. 117(1985) 15-1197.
[11] J.M Aizpurua, M. Juaristi, B. Lecea, C. Palomo, Tetrahedron. 41(1985) 2903-2911.
[12] F. Yoneda, K. Suzuki, Y. Nitta, J Org Chem. 213 (1967) 32-727.
Sh. Ghammamy, J. Iranian Chem. Res. 5 (3) (2012) 173-176
176
[13] K. Nakagawa, S. Shiba, M. Horikawa, K. Sato, H. Nakamura, N. Harada, F. Harada, Synth Commun. 10
(1980), 305-311.
[14] H. Firouzabadi, N. Iranpoor, F. Kiaeezadeh, J Toofan Tetrahedron. 5 (1986) 719-725.
[15] V. Ley, A Clive.Mirholz, Derek H.R. Barton, Tetrahedron. 37 (1981) 213-223.
[16] H.A. Muathen, Ind J Chem. 30B (1991) 522-524.
[17] A. Mckillop, D. Koyuncu, A. Krief, W. Dumont, P. Renier, M. Trabelsc, Tetrahedron Lett. 13 (1990)
31-5007.
[18] H. Tamamura, A Otaka, J. Nakamura, K. Okubo, T. Koide, K. Ikeda, N. Fujii Tetrahedron Lett. 34
(1993) 4931-4934.
[19] N.A Noureldin, M. Coldwell, J. Hendry, D.G Lee, Synthesis. (1998) 1587-1595.